Dive Into the Deep Web

Alex Winter

Alex Winter, best known for portraying Bill opposite Keanu Reeves' Ted in the 1989 classic Bill & Ted's Excellent Adventure, has long been fascinated by electronic communities. He even directed a documentary, Downloaded (2012), on filesharing. His latest documentary, Deep Web, premiered on the Epix channel in late May. It tells the story of Silk Road, a website that flourished from 2011 until 2013, when the feds shut it down.

Silk Road was a platform for buying and selling mostly illegal items. Earlier this year its alleged creator, Ross Ulbricht, was found guilty in federal court on various charges related to running the site. In early May, Senior Editor Brian Doherty spoke with Winter about the film.

Q: Are you telling a story with an end—Silk Road gone—or one just beginning?

A: Of course it's just the beginning. The parallels between Silk Road and Napster are striking. You have this very simple but brilliant technological advancement, with Silk Road combining Bitcoin and Tor and growing into a scalable anonymized community. The essence was more threatening to government than the drugs, like that community ease of use with Napster was more threatening to institutional power than just piracy per se. The second big similarity is in Silk Road you had a central server. Just like with Napster, that became a weakness because it's easier to shut down.

Like with Napster, copycats appeared, most of them terrible, but some are showing up that are very successfully moving toward a decentralized market, like with BitTorrent, and that will be extremely difficult to stop. Silk Road is the beginning of the era, not the end. And even with Ulbricht's story, revelations about [criminality on the part of] the federal agents [investigating him] show that what happened with Ross, other things might come out. The book might get slammed on him, but his family will work tirelessly appealing.

Q: You got interesting stuff from FBI agent Chris Tarbell, the guy who allegedly found the Silk Road server via a security error on the site. Was there anything tricky about getting the government's side?

A: I was happy that I didn't get clichéd table-pounding demonizing of the Internet and privacy. I got a genuine examination of a conundrum. You can say you want to dismantle privacy and encryption and anonymity, but you are making yourself more vulnerable [as a society] if you do that. It's just a fact, [these technologies] require more legwork for law enforcement, in the same way it requires legwork if you go up to a house with a lock on the door. But that doesn't mean we shouldn't be allowed to have locks.

Q: Are you optimistic or pessimistic about the future of the liberty Silk Road represented?

A: Andy Greenberg [of Wired] said it well in the movie: It will be a continual game of cat and mouse, and in the end the mice will win, but the cats will be well-fed. Despite the continual fist-waving and invective [over everything] from Napster through the Arab Spring through WikiLeaks through Silk Road, we have been expanding freedom and using technology to create social change, inform and change politics, and connect people—whether in totalitarian regimes or in perceived free cultures like ours. While institutional pressure against those technologies and movements has been increasing, those movements and technologies have been expanding regardless.

Things like Silk Road that help erode the horrendous drug war will continue to change policy on a big level. I'm not all rosy or Pollyanna about the Net. It's not all great. Horrible things go on, but I am supportive of using technologies to democratize culture and change policies that need to be changed.